WO2010031708 Novel ortho-aminoanilides for the treatment of cancer

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Scaffold: aminoanilide

Biological target:

Histone deacetylase: HDAC



Steps Conditions Reactions
a TBDMSCl / imidazole / DMF TBDMS protection
b t-BuOK / DMF Nucleophilic substitution
c Pd2(dba)3 / Tri-o-tolylphosphine / Et3N / DMF Heck reaction
Steps Conditions Reactions
a EDCI / HOBt / DIEA / DCM Amide synthesis (EDCI coupling)
b TBAF / THF TBDMS deprotection
c MsCl / DIEA / DCM  Mesyl synthesis
d (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane / DIEA / DCM Tertiary synthesis (nucleophilic substitution)
e HCl  /MeOH Boc deprotection
Steps Conditions Reactions
a NaH / DMF / Toluene Nucleophilic substitution
b H2SO4 / H2O Carboxylic acid synthesis (Ester hydrolysis)
c SOCl2 / MeOH Ester synthesis (Esterification)
d Pd2(dba)3 / tri-o-tolylphosphine / Et3N / DMF Heck reaction
e LiOH / MeOH / H2O Acid carboxylic synthesis (Ester hydrolysis)
f HATU / Et3N / DCM Amide synthesis (HATU coupling)
Steps Conditions Reactions
a formaldehyde / Bu4NCl / K2CO3 / DMF Alkene synthesis
b THF Tertiary amine synthesis (nucleophilic substitution)